


Sharp Dressed Man

by BewareTheIdes15



Category: Supernatural
Genre: Crossdressing, Lingerie, M/M, Sibling Incest, Weechesters, Wincest - Freeform
Language: English
Status: Completed
Published: 2011-07-04
Updated: 2011-07-04
Packaged: 2017-10-21 01:12:50
Rating: Explicit
Warnings: Underage
Chapters: 1
Words: 4,035
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/219255
Author URL: https://archiveofourown.org/users/BewareTheIdes15/pseuds/BewareTheIdes15
Summary: <blockquote class="userstuff">
              <p>There are probably any number of totally appropriate responses to walking in on your sixteen-year-old brother in lace panties and fishnet, thigh-high stockings. Getting stupidly hard is not one of them.</p>
            </blockquote>





	Sharp Dressed Man

Dean shoves the Impala's keys deep into his jacket pocket, rubbing his hands through the lining against his t-shirt to build up some friction-heat. His breath puffs out in little clouds as he flips through the stack of mail on the kitchen table and quickly decides it's not worth it - he can look for credit card applications once he's got feeling back in his fingers. No surprise that their stupid rental didn't come with a radiator or anything, but that doesn't mean he can't be bitter about it.

He toes off his boots on the cracked, beige-and-blue linoleum, stopping to rewash his hands for the inevitable lingering traces of axel grease - fucking water heater barely works either. Who the hell was supposed to live this way in fucking October in Massachusetts? - and finally hustles himself down the wood-appliquéd hallway. He and Sam have a space heater in their tiny shared bedroom that Dean's been having lewd fantasies about all afternoon in the freezing garage and he feels an inordinate thrill of anticipation for that small creature comfort as he grabs the rattling door knob.

There are probably any number of totally appropriate responses to walking in on your sixteen-year-old brother in lace panties and fishnet, thigh-high stockings. Getting stupidly hard is not one of them.

Dean's standing stock still in the doorway, the blast of warm air from the decades-old space heater mingling with the chill of the hallway behind him. He's reasonably certain that he came in here for a reason, but apparently along the way he stepped into an alternate dimension or something where Sam not only dresses in women's lingerie but looks way too fucking hot in it.

All that hard, lean muscle that the kid just can't seem to stop putting on, rippling over his chest and down into the waistband of those lacy black panties. That pert little ass that's always hidden under his fucking baggy jeans - you could bounce a damn quarter off that thing and get back two dimes and a nickel - and those long, toned, long long long legs... hell, did Sam shave his legs?

"Dean!" Sam shrieks like a girl too, maybe it's the clothes. It suddenly occurs to Dean that he's kinda been standing in the doorway staring for an indeterminate amount of time and his first instinct is to make sure his jacket is still covering his now throbbing hard-on. It is. Sweet.

"What are you..." Dean babbles intelligently, using all of his effort to look at Sam face instead of the motherfucking acres of skin on display - when the hell did Sam get that hot? Of course, looking at Sam's face doesn't help much because the kid is all done up there too. Some kind of dark eye shadow or liner or something around the rims of his eyes and from the look of it, mascara too, accenting that slight, foxish tilt that they have and practically lighting up a blinking neon sign - 'Come fuck me. Hard. All night long. I want it'. Dean really needs that sign to shut the hell up.

"You said you were gonna be working late," Sam snaps, like Dean getting home from the garage early is the fucking problem with this situation.

"This is what you do when I'm not around!" Dean's almost completely sure the anger in the voice is about the women's underwear and not the 'when I'm not around' part. Almost completely.

"It's a Halloween party, Dean! I told you about this!" Sam rolls his made-up eyes and turns his back on Dean, rummaging around in a black plastic bag on the floor. Dean's going to come up with a brilliant response to that just as soon as Sam stops being bent over like an embossed invitation. Ok, maybe he's sorta remembers Sam saying something about something with a party...

"I... uh... You're going like this?" Protectiveness swells up in Dean on instinct because no fucking way is anybody else getting to see Sammy look like that. And not because Dean wants his little brother all to himself. God, this is a problem.

"No!" Sam huffs in his 'you're the dumbest person alive' voice, "It's a drag ball thing. The guys dress as girls and the girls dress as guys. I'm wearing this." Sam holds up a small stip of leather he can only assume is a skirt and some kind of black and red contraption that scares the hell out of Dean. If this was supposed to comfort him, it's failing miserably.

"No, you're not," is out of Dean's mouth before his brain registers that that's the worst possible thing to say to Sammy.

But Sam's already pulled out the 'fuck you' face - it's a lot prettier with the makeup - which means he's digging his heels in on this one and… oh God, are there going to be heels? Do they make heels in Sam's size? Shit! How the hell had Dean let this whole 'Sam's a hot motherfucker' thing sneak up on him?

"Bite me," Sam says, stepping into his tiny little leather skirt and zipping it up in the back and... do they have time for a quick jerk off break, because Dean would be much better at having this conversation if there was some actual blood in his brain.

"I- you didn't say the party was at night," Dean finally retorts, slamming the bedroom door shut as if that's going to stop Sam. At least the room will stay warm.

"When the hell else would a Halloween party be, genius? Kelsey and them are gonna be here soon, I'll be back before midnight, I promise." Sam slides his arms into what must be the straps of the scary red and black thing. Oh! Once it settles against Sam's back it's pretty obviously a corset which... oh. This is not good. Well, depending on who you ask - Dean's dick seems to think it's fantastic.

The black laces are undone down the back so that even when Sam's got all the little hooks done in the front, it's not really form fitting. That is until Sam starts reaching behind him and trying to tug them tight. Who the hell gave the kid these clothes, Satan? The answer, when Dean actually asks the question, turns out to be 'Tiffany' which sounds pretty damn Satanic as far is Dean's concerned. He makes a mental note to check her family history for anything suspicious.

Sam makes a few obviously disgruntled noises struggling with his hooker top before he finally gives in and says, "Could you..."

This, of course, is the point in the argument where Dean should refuse to help and make Sam fucking stay home and take off the outfit from Dean's personal nightmare of temptation. Dean, of course, does not do this, because Dean's discovered over the years that when his dick gets involved - and oh buddy, is it ever involved - his decision-making skills turn to shit.

What Dean _does_ do, is take the couple of steps over the worn-down, vomit-colored carpet and start pulling on the laces of his little brother's corset. He has the most screwed up life on the planet.

The corset is made of some kind of stretchy satiny shit that's already body-warm when Dean's fingers accidentally brush it as they pull the laces tight. Sam's skin, though, that's even better than the shiny fabric when his knuckles drag over the exposed flesh beneath the laces. It's got a soothing heat to it, like a long, hot bath on sore muscles and it's buttery soft and Dean doesn't want to lick it, not even the tiniest bit, except for the way that he totally and completely does. Kind of a lot.

There's not a lot of give to Sammy's body - no trace of baby fat anymore - so even once the laces are tied tight enough that Dean's not sure how his brother's breathing, it's not exactly the shape the corset's made for. It's still fucking hot though, just that little nip in that waist, that tiny bit of curve.

Dean's not sure when his hand decided it would be a good idea to run up and down that small slope, sliding the length of Sam's side over and over. It's way too late to stop once he realizes it, though, because Sam's frozen in place, definitely not breathing and Dean has a feeling it doesn't have anything to do with the slutty-ass top from hell.

He jerks his hand away fast as if that's going to make a difference and steps back, banging into the foot of Sam's bed in the process and ends up flopped back on the thin, Sam-scented sheets.

It's not until then that he notices what Sam was doing all of that time he was busy perving like a freak over his little brother's skin. Sam turns to him, smoky eyes shell-shocked, and absently puts the cap on a tube of red lip gloss.

Sam has kind of thin lips normally, a fact that they go back and forth about with Sam teasing Dean about his blow-job lips and Dean saying Sam's just jealous that he doesn't have them to suck his boyfriends off with. Not that Dean ever seriously considered Sammy giving anybody a blow. Until now. Now, with his lips all shiny and cherry red and looking more than a little well-fucked already Dean can't seem to think about anything other than Sam giving blow jobs. To Dean. Oh God.

He's so busy staring at the way Sam's mouth is just begging to be ridden hard that it takes him a minute to notice how his brother's tiny leather skirt is tented in the front. In fact, he doesn't notice it at all until Sam crawls over the foot of the bed and right up between Dean's knees. That's also about the time that he realizes that his legs are splayed out and his raging hard-on is pretty fucking obviously gnashing at his fly for freedom.

Sam opens his mouth to say something and then snaps it closed again, repeats the process a couple more times and if they weren't right on the verge of some kind of major make-or-break moment it would probably be funny as hell. Sammy's pink tongue darts out, getting his shiny red lips even shinier and oh just fuck it; Dean doesn't do this broody crap.

He surges up to a sitting position, his lips close enough that some of Sam's sticky gloss rubs off on them and then he hears the car horn outside breaking through the sex-heavy tension vibrating between them like it was made of spun sugar.

"Shit, Kelsey," Sam breathes, not moving away. Their lips drag against each other in the viscous pull of the gloss, tantalizing almost kisses that make Dean want to groan because if this moment's lost he's going to spend the rest of his natural life jacking off to what could have happened. "I- I gotta..." Sam hesitantly begins to pull away, unidentified things inside of Dean cracking into splintery-sharp pieces as he goes and has Dean mentioned fuck it? Because, yeah, fuck it.

His hands make a satisfying slap as they clamp down around Sam's leather covered ass and it's not even a challenge to flip his stunned little brother onto the creaky mattress, no matter how big he's gotten.

"Sorry, Sammy. Looks like you're staying in tonight," he growls, shoving a thigh between Sam's. "Must not have wanted to go very bad anyway, walking around here looking like that."

Sam's little brother instincts are still spot on, even if his voice is hollow and shocked. "N-not looking like anything," he protests.

"Looking like hot," Dean's tongue snakes out to lap at the too-slippery line of Sam's lower lip, "And you're not leaving 'til I get a taste."

Their lips crash together and he's not really sure if he pushed for it or Sam did, but they're kissing now and it's pretty damn good. The kid's got no technique and Dean mentally ratchets down the number of girls he figures Sam's had a chance to make out with, because he's mostly just playing follow the leader with whatever the hell Dean decides to do to him, which isn't bad, but it's kinda distracting.

Dean pulls back just enough to pant, "Stop thinkin' so hard, gonna like anything you do". Which is completely true because technique or not, kissing Sam beats out any other rush Dean's ever had, rockets right to the top slot and just keeps on going because it's _Sam_. And why the hell not, right? This is pretty much the one and only thing they've never shared and suddenly the only thing that feels wrong about it is that Dean wasn't there to show Sam how to kiss the first time, that he doesn't know every single one of the gorgeous little sounds Sam's pouring into his mouth now by heart.

He rocks his thigh up between Sam's legs, rucking up the leather skirt until there's lace grinding against his jeans and just the thought of Sam's big hard dick - and it's gotta be fucking big, no way the kid's not proportional at least - straining against that dainty fabric... he's just gotta get a hand on it.

Sam squeaks when he does, hips pumping up automatically and the other number in Dean's head ratchets on down too, which could very well mean that little Sammy's a fucking virgin and there's no way that should make this hotter - no way he should even be capable of getting hotter - but it so does. His Sammy, a sweet little cherry, ripe for the picking.

Oh, also - yeah, even better than proportional. Jesus H. Christ.

Dean leans up on an elbow - relinquishing Sam's mouth even when his brother whines high in his throat - and pulls back the skirt to look at that long, hot shaft wrapped up in black lace and his own thick fingers. Well, not completely wrapped up, there are still several inches poking above the waistband, dripping messily onto Sam's smooth skin.

"Damn, baby boy, fucking' huge," he murmurs and while most guys would glow like a goddamn light bulb under that kind of praise, Sam just blushes right up to the tips of his ears. It makes Dean want to kiss him all over again, so he does, winds his tongue right into Sam's mouth and licks at the tender underside of his tongue.

Sam nips, ever so softly at Dean's tongue as he pulls out and he grinds his aching dick against Sam's hip as encouragement.

"Yeah, like that," Dean moans, "Not gonna break me, Sammy, go for it."

Apparently that was all the kid had been waiting for because he just goes to fucking town, nipping and kissing at everything he can reach, capturing Dean's bottom lip and suckling on it until Dean is 100% certain that he's going to cream his pants if Sam doesn't stop that in the next five seconds. Fortunately, Sam's a sixteen-year-old boy, so all it really takes is one firm pull up the length of his cock to throw off his game and get his neck arched back on a moan. And that's a request if Dean's ever seen one.

He bites and licks at the long, exposed column of Sam's throat, those sweet sounds vibrating against his lips and turning his blood up from simmer to boil. He gets a hand wound up in Sam's hair, just beginning to dampen with sweat, silky-soft as he pulls gently to keep Sam's head arched back just like that and his brother whines pitifully. He plants one good, hard bite just to see if maybe Sammy likes it a little bit rough too and the kid's dick twitches so hard in his hand that for second Dean thinks his brother's about to come. Sam holds back though, teeth gritted under kiss-swollen lips, sticky gloss smeared all over the place.

Looking down the long line of Sam's body, mussed hair and makeup running with sweat, tan skin peaking out over the lines of the silky corset and through the little holes in the fishnets, leather and lace and big, hard cock... This is the single most debauched thing Dean has ever seen in a long and prestigious career of debauchery. Fuck, it's good.

Dean rips open his fly, pulls down both his jeans and briefs until his own thick erection - practically cheering with the joy of being free - is out, sliding between Sam's legs to press their lengths together.

Sam hisses and squirms like he's really going to lose it this time, but he still doesn't and Dean has to give it to the kid for stamina, especially with no experience. He slips down the lace panties until the waistband is snugged beneath Sam's tight, heavy balls, taking a moment to roll them around in his palm and learn the soft heft while Sammy keens. Then finally, blissfully, Dean thrusts velvety hot flesh together, the head of his dick sliding through the puddle of Sam's precome making Dean groan even louder.

Sam thrashes, hands slamming down onto Dean's back and he's still wearing the fucking jacket so he can't even feel it right but he can hear Sam's fingernails scratching over the leather and it sends a sympathetic shiver down his spine anyway.

"You like that, Sammy?" he asks smugly - hey, he's fucking entitled to be with a hottie like Sammy writhing under him - and tightens his grip back up on Sam's hair, keeping his little brother's body strung taut. He makes the thrusts uneven, some soft, some slow, enough to keep Sam off guard for when he really give it his all for a couple of gos.

"Yes, God, fuck me," Sam whimpers, totally lost in it, and fuckityfuckfuckinfuck Dean has to bite down on his tongue to keep from losing it at the unexpected jolt of hearing something like that come out of Sam's mouth for him.

"Shit! Shit! What're you doin' to me Sam?" he mutters, jerking on Sam's hair a little for emphasis and the kid just rolls his hips for it like it's the best damn thing he's ever felt. Dean's carefully picking back up the thrusts, but there's no way he's going to hold back for long now, not with the idea of Sam's tight little hole stretched wide around his cock rolling around in his head. "Not yet, baby boy. Soon, fuckin' real soon, but not yet."

His balls are trying to kill him for turning down a sweet, untouched piece of ass like Sam's - bet he'd be so hot, so tight, probably sweet and pink like a little cunt, rippling and squeezing until it almost hurts but it's so damn goo- ungh, gotta stop thinking that! - but he's too revved up to do it right and when he takes Sam - and oh hell yes, he is so going to take him - he wants it to be so fucking good Sam'll never want anything more than Dean's dick up his ass every day for the rest of his life. So he just fucks harder into Sam's skin, their cocks trapped between their bodies, Sam's hips rolling up in the rhythm now too - always was a fast learner - as he bites his swollen lips and paws at Dean's back.

"Please, please, please," pours out of Sam's mouth and Dean's sure even he doesn't know what he's begging for. Dean gives it to him anyway, gives everything he can like this, pushes harder, faster, tugs on Sam's hair until his shoulders are bowed up off the bed and brings them together tighter until all that's coming out of Sam's mouth is a strained litany of 'ah, ah, ah, ah, ah' before his mouth opens on a silent scream and he spills slick heat between them.

Dean's right on his heels and his cock sliding through the wet fire of Sam's come is more than enough to push him over, biting down on Sam's collar bone as white fireworks go off behind his eyelids, the incendiary glow of orgasm tingling right down to his fingertips.

Sam makes a lot of breathy, barely audible noises in his chest that Dean only hears because the side of his face is plastered to the sweat-sticky skin above the line of red and black satin. It takes him a minute to figure out that his fingers are still tangled up in his brother's hair, tingling like he'd had them in a white-knuckle grip around the soft strands. He pets through the damp brown curls instead, measuring the slowly steadying tempo of Sam's heartbeat against his cheek.

The room's too hot now, sweat pricking on his scalp and soaking through his clothes with the combined heat of their bodies, but moving's pretty much the last thing he feels like doing.

"I think your friends left," he says, not bothering to lift his head from Sam's broad, heaving chest. He can feel the pluck of pressure as Sammy's long fingers idly pick at the upturned collar of Dean's jacket.

"Fuck them," Sam's retort is slow and lazy and sounds as happy as Dean feels.

"You better not, bitch," he jokes anyway, poking Sam's corseted side.

"What're you gonna do about it, jerk?" Sam laughs, bucking his hips up a little so their soft dicks slide together through slowly cooling come and they both groan at the sensation.

"Better watch who you're stepping to, baby boy, you're the one in a skirt." With a heave of effort, Dean slowly forces himself to roll off of Sam, overheated body protesting the loss immediately. Sam looks wrecked, sweaty and flushed with his hair all over the place and a glaring set of teeth marks on his collar bone that aren't going anywhere for days. His legs are still spread, a milky mess of fluid all over his groin, and Dean's beginning to seriously doubt if whatshername is even going to want her clothes back, assuming Dean can be persuaded to let Sam part with them.

"Yeah, but you're the one with a hard on for me in a skirt," Sam laughs easily and Dean would almost think he was high, except the universe would probably implode or something if Sam was even in the same room with someone smoking weed. Then again, Sam had just put on women's underwear and rubbed off on his big brother, so maybe Dean wasn't giving the universe enough credit.

Unusual for Sam, he doesn't try to cover up - not that there would be much point after all of that, but Sammy's kind of funny about things sometimes - just lays there all loose and satisfied and it's a good look for the kid. Dean could get used to seeing him this way, could really get used to making him look this way - maybe without all the chick's clothes and the makeup, at least most of the time.

Sam pops the hooks on the front of the corset and rolls over until he's most of the way on top of Dean.

"Dude! You're getting jizz on my jeans!" he complains, shoving at Sam's shoulders, but the kid's like a baby possum or something, latched on for dear life.

"Deal with it," Sam shrugs, obviously settling in for a little nap. Dean can't help but grumble because the dirty, hot, naughty sex stuff was one thing, but cuddling after is a whole different deal.

"Big freakin' girl," he mutters, settling his arms around Sam anyway. Not like he hasn't slept with his little brother all over him a few thousand times before. And now it might be just a little bit sexy.

"Got the look for it," is all Sam says but Dean can feel he's grinning against his ribs. He runs his fingers through Sam's messy hair, scratching softly over his scalp the way his brother always liked. Sam hums and noses at Dean through his t-shirt for a minute before Dean feels him relax completely. He presses a kiss to the crown of Sam's head and holds him close, letting the heat and the familiar smell of Sam lull him to sleep.


End file.
